Month: April 2022

Reference of 107351-82-6, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 107351-82-6, name is 2-Bromo-5-phenylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 3 Synthesis of 2-[4-(5-phenylpyridin-2-yl)phenyl]-4,6-di-m-tolyl-1,3,5-triazine Under a stream of argon, 3.0 ml of a hexane solution containing 4.2 mmol of butyl lithium was slowly added to 80 ml of tetrahydrofuran cooled to -78C in which 1.58 g of 2-(4-bromophenyl)-4,6-di-m-tolyl-1,3,5-triazine obtained in Reference Example 2 had been dissolved. After stirring at -78C for 15 minutes, 0.87 g of trimethyltin chloride was added thereto and stirred at -78C for 45 minutes and then at room temperature for 30 minutes. After evaporating and drying tetrahydrofuran under a reduced pressure, 120 ml of toluene in which 1.07 g of 2-bromo-5-phenylpyridine had been dissolved and 0.44 g of tetrakis(triphenylphosphine)palladium(0) were added to the thus obtained solid and stirred under heating reflux for 3 days. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was recrystallized from dichloromethane-methanol. The thus obtained crude product was purified by a silica gel column chromatography (eluding solution hexane:chloroform = 3:2 to 1:1) and then again recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2-[4-(5-phenylpyridin-2-yl)phenyl]-4,6-di-m-tolyl-1,3,5-triazine (0.14 g, yield 8%). Its melting point is shown in Table 4. Distinct point of glass transition was not observed. 1H-NMR (CDCl3): delta 2.48 (s, 6H), 7.33-7.51 (m, 7H), 7.56-7.64 (m, 2H), 7.84-7.99 (m, 2H), 8.21 (d, J=8.5 Hz, 2H), 8.49-8.58 (m, 4H), 8.84 (d, J=8.6 Hz, 2H), 8.95 (d, J=1.7 Hz, 1H). 13C-NMR (CDCl3): delta 21.6, 120.9, 126.3, 127.0, 127.1, 128.3, 128.6, 129.2, 129.5, 133.3, 135.3, 135.6, 136.2, 136.9, 137.4, 138.3, 142.4, 148.2, 155.2, 171.2, 171.8.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 107351-82-6, 2-Bromo-5-phenylpyridine.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH CENTER; EP1930329; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1018505-59-3 ,Some common heterocyclic compound, 1018505-59-3, molecular formula is C11H18N4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 3-chloro-7-(3, 5-dimethoxyphenyl) isoqinoline (50 mg, 0.167 mmol) , 5-(4- ethylpiprazine-l-yl) pyridine-2-amine (38 mg , 0.183 mmol), X-Phos ( 8 mg, 10 mol% ) and cesium carbonate (108.4 mg, 0.334 mmol) in Toluene (4 mL) and t-BuOH (1 mL) (4: 1) argon was purged for 20 min. Then was added Pd(OAc)2 (3.76 mg, 10 mol%) again argon was purged for 5 min. The reaction mixture was heated at 120C for O/N. The reaction mixture was cooled to room temperature and filtered through celite pad and filtrate was concentrated under reduced pressure. Product was purified by column chromatography on silica gel column using DCM: MeOH: NH3 aq. (94:6: 1%) as an eluent to afford 7-(3,5-dimethoxyphenyl)-N-[5- (4-ethylpiperazin-l-yl)pyridin-2-yl]isoquinolin-3 -amine (20 mg) as a brown solid. 1H NMR (400 MHz, CDC13) delta 9.00 (s, 1H), 8.14 (s, 1H), 8.06 (d, J = 2.5 Hz, 1H), 8.00 (s, 1H), 7.79 (dd, J = 19.3, 8.6 Hz, 2H), 7.42 (s, 1H), 7.31 (dd, J = 8.9, 2.7 Hz, 1H), 7.10 (d, J = 8.9 Hz, 1H), 6.83 (d, J = 1.9 Hz, 2H), 6.49 (s, 1H), 3.88 (s, 6H), 3.25 – 3.14 (m, 4H), 2.66 (d, J = 4.4 Hz, 4H), 2.50 (q, J = 7.1 Hz, 2H), 1.15 (t, J = 7.2 Hz, 3H).M/Z: 469.58, M+l : 470.4, tR= 2.1 min. (System 2)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018505-59-3, its application will become more common.

Reference:
Patent; EVOTEC (UK) LTD.; MC CARTHY, Clive; MILLS, Matthew; WO2014/44846; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65873-72-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.65873-72-5, name is 6-Methoxynicotinaldehyde, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.

Reference Example 28Step 15-chloromethyl-2-methoxypyridine (Compound A80)2-methoxy-5-pyridinecarbaldehyde (137 mg, 0.999 mmol) was dissolved in methanol (5.0mL). To this, sodium borohydride (37.8 mg, 0.999 mmol) was added at 0C, and the mixture was stirred for 1 hour. To the reaction mixture, a saturated ammonium chloride aqueous solution was added, and extraction with ethyl acetate was performed twice. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the residue was dissolved in dichloromethane (5.0 mL). To this, triethylamine (278 muL, 2.00 mmol) and methanesulfonyl chloride (116 muL, 1.50 mmol) were added, and the mixture was stirred overnight. After a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, extraction with chloroform was performed twice. The organic layer was dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the residue was purified by silica gel column chromatography to give Compound A80 (116 mg, yield: 74%). ESI-MS: m/z 158 [M + H]+; 1H NMR (CDCl3)delta(ppm): 3.94 (s, 3H), 4.55 (s, 2H), 6.76 (d, J = 8.4 Hz, 1H), 7.62 (dd, J = 2.4, 8.4 Hz, 1H), 8.15 (d, J = 2.4 Hz, 1H).

Statistics shows that 65873-72-5 is playing an increasingly important role. we look forward to future research findings about 6-Methoxynicotinaldehyde.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2308880; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60753-14-2 ,Some common heterocyclic compound, 60753-14-2, molecular formula is C9H13NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: To a solution of 3-(pyridin-4-yl)propan-1-ol (151mg, 1.1mmol), 2-(3-bromophenylthio)pyridine-3-ol (5) (282mg 1.0mmol) and triphenylphosphine (289mg, 1.1mmol) in THF (2.0mL) was added diisopropylazodicarboxylate (222mg 1.1mmol) at 0C and stirred at ambient temperature. After 5h, the mixture was evaporated, diluted with EtOAc (15mL), and extracted with 10% HCl solution (2×15mL). The aqueous phase was then basified to pH 12 with K2CO3 and extracted with EtOAc (2×15mL). The organic phase was washed with brine (2×5mL), dried (Na2SO4), and evaporated in vacuo. The residue was subjected to flash column chromatography (EtOAc-hexane gradient) followed by crystallization (Et2O) to afford title compound 3 as a white crystalline solid (390mg, 97%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60753-14-2, its application will become more common.

Reference:
Article; Kato, Yoshihiro; Kawasaki, Motoji; Nigo, Tomohiro; Nakamura, Shunya; Fusano, Akira; Teranishi, Yasuhiro; Ito, Mari N.; Sumiyoshi, Takaaki; Bioorganic and Medicinal Chemistry; vol. 21; 18; (2013); p. 5851 – 5854;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 145335-90-6 ,Some common heterocyclic compound, 145335-90-6, molecular formula is C8H7ClN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Method 2: To imidazo[l,2-alpha]pyridine-8-carboxylic acid hydrochloride (15.0 g, 76 mmol), toluene (80 mL) was added followed by thionyl chloride (17.4 g, 146 mmol). To the resulting mixture, N^N-dimethylformamide (1.15 mL) was added. Gas evolution was noticed and the mixture was stirred at ambient temperature for 30 min and then was heated to 50 0C overnight (18 h). The reaction mixture was then cooled to room temperature for 30 min and the product was filtered and washed with isopropyl acetate (40 mL) followed by ethyl acetate (40 mL). The white solid was dried under reduced pressure to afford the title compound (13.4 g, 82%). The compound was used without further purification in step E.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 145335-90-6, Imidazo[1,2-a]pyridine-8-carboxylic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2009/23253; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 821791-58-6 ,Some common heterocyclic compound, 821791-58-6, molecular formula is C9H10ClNO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step C: Preparation of 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid: To a solution of 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (0.925 g, 4.29 mmol) in a 4:1 mixture of THF:MeOH (20 mL) was added a 1 M solution of LiOH (8.6 mL). After stirring for 30 minutes, the reaction mixture was acidified to pH 1 with 10% HCl and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure to give 0.732 g (91%) clean desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,821791-58-6, its application will become more common.

Reference:
Patent; Marlow, Allison L.; Wallace, Eli; Seo, Jeongbeob; Lyssikatos, Joseph P.; Yang, Hong Woon; Blake, James; US2005/256123; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1026796-81-5 ,Some common heterocyclic compound, 1026796-81-5, molecular formula is C7H7BrN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a 15 mL vial was added N-(4-bromopyridin-2-yl)acetamide (205.8 mg, 0.957 mmol), (3-fluoro-4-hydroxyphenyl)boronic acid (239 mg, 1.531 mmol), and Na2CO3 (1.435 mL, 2.87 mmol) in dioxane (3 mL) under nitrogen to give a colorless solution. 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, toluene (39.4 mg, 0.048 mmol) was added under nitrogen. The vial was sealed and heated at 130 C (microwave) for 2 h. The mixture was partitioned between water and EtOAc. The layers were separated. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure to obtain N-(4-(3-fluoro-4- hydroxyphenyl)pyridin-2-yl)acetamide (200 mg, 0.812 mmol, 85% yield) as a tan solid. LCMS (ESI) m/e 247.0 [(M+H)+, calcd C13H12F1N2O2, 247.1]; LC/MS retention time (method A): tR = 1.51 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1026796-81-5, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DZIERBA, Carolyn Diane; DITTA, Jonathan L.; MACOR, John E.; BRONSON, Joanne J.; WO2015/153720; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1142197-14-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1142197-14-5, name is 2-Bromo-5-cyclopropylpyridine. A new synthetic method of this compound is introduced below.

Step 1 : 2-bromo-5-cyclopropylpyridine -oxide (245) [0747] To a solution of 2-bromo-5-cyclopropylpyridine (2.0 g, 10.1 mmol) in CHCI3 (10 mL) was added m-CPBA (2.62 g, 15.2 mmol). The reaction was stirred at room, temperature overnight. The mixture was diluted DCM and washed with 5% aq. NaHCC solution and brine. The organic layer was dried over anhydrous NaiSCH, filtered and concentrated. The residue was purified by column chromatography on silica gel eiuted with PE/EtOAc (30: 1 to 1 : 1) to give compound 245 (2.12 g, 98.6 % yield) as a white solid. LC/MS (ESI) m/z: 214 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1142197-14-5, 2-Bromo-5-cyclopropylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (386 pag.)WO2017/35355; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 121643-44-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, molecular weight is 177.1239, as common compound, the synthetic route is as follows.

Intermediate 1 : 5-Bromo-2-methoxy-3-trifluoromethyl-pyridineTo 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5- dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

Statistics shows that 121643-44-5 is playing an increasingly important role. we look forward to future research findings about 2-Methoxy-3-(trifluoromethyl)pyridine.

Reference:
Patent; NOVARTIS AG; FERNANDES GOMES DOS SANTOS, Paulo Antonio; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SOLDERMANN, Nicolas; STOWASSER, Frank; TUFILLI, Nicola; ZECRI, Frederic; WO2013/1445; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol, the common compound, a new synthetic route is introduced below. Quality Control of (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol

A mixture of compound F1 (3.38 g, 13.9 mmol), 2,6-dichloro-p-cresol (3.69 g, 20.9 mmol), ADDP (5.26 g, 20.9 mmol) and PBu3 (85%, 10.3 mL, 35.4 mmol) in toluene (200 mL) was heated to reflux for 2 h. The mixture was allowed to cool to rt, and was diluted with heptane. The mixture was filtered, washed with heptane, and the filtrate was evaporated under reduced pressure. The residue was diluted with CH2Cl2, and this mixture was washed with aq. 1M NaOH (2×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2Cl2/heptane 4:1?CH2Cl2) yielded the title compound (5.46 g, 98%). LC-MS: tR=0.91 min; ES+: 403.00.

The synthetic route of 946002-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Actelion Pharmaceuticals, Ltd.; US2009/88457; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem